Fungicidal composition of undecylenic acid derivatives



United States Patent 2 Claims. (51. 167-22) It has been known previously that the monoethanolamide of undecylenic acid has a fungicidal effect and it has been proposed to use this monoethanolamide derivative as a fungicidal agent.

It has now been discovered that certain other amidic derivatives of undecylenic acid described and claimed hereinafter have fungicidal effects and that these amidic derivatives are active not only against fungi but also against bacteria and other microorganisms.

In general these undecylenic acid derivatives are of W efIect against gram negative bacteria but are rather effective against many gram positive organisms. They are also effective against many molds and yeasts and against many fungi.

The undecylenic acid derivatives used in this invention show consider-able advantages over the undecylenic acid monoethanolamide, either because in some cases their etiectivness is greater and may embrace a greater range of organisms, or because in other cases the product possesses characteristics which make it more convenient in use, as for example, greater solubility in water.

The present invention relates to a process for inhibiting the growth of microorganisms, killing microorganisms and for the relief and treatment of diseases resulting from the action of microorganisms, comprising the use for said purposes of undecylenic acid derivatives corresponding to the general formula CmHmC O.N.(CHz) (CHzO) yH wherein the group C ,,H CO is the acyl derivative of undecylenic acid, R is selected from the group consisting of alkyl and alkylol, and containing up to 4 carbon atoms; n stands for an integer of 1-4 and y is an integer in the range of 1-30.

The scope of the present invention includes compounds as defined above when these are associated with excess alkylolarnine in the form of such a complex. Indeed, since these complexes are often more soluble in water than the pure amide they may very well be useful for incorporation in aqueous compositions. An example of such a material is the product obtained by condensing undecylenic acid with diethanolamine in the proportion of 1 gram molecule of the former to 2 gram molecules of the latter at 150 to 170 C.

The products of this invention may also be incorporated in dusting powders or may be applied to the skin in some cases as solutions in an organic solvent, for example, ethyl alcohol. They may be incorporated in creams or lotions in which other materials commonly used in cosmetics or pharmacy are also present. They may also be incorporated in compositions based mainly on wax, oil or grease, for example, lipstick, brilliantines or water-in-oil emulsions such as cold cream or some types of hair cream. The amides may also be incorporated in shampoos or detergent preparations intended to cleanse the hair or skin. They may also be incorporated in soap preparations including the conventional bars or tablets, liquid soaps, shaving creams, and the like. While it is primarily intended that the amidic derivatives described shall be used for cosmetic or pharmaceutical purposes, it will be appreciated that they may be incorporated in a wide range of preparations not necessarily cosmetic or pharmaceutical, where a germicidal or fungicidal action is desired. They may further be incorporated in preparations not intended to act as fungicides or germicides but where a preservative is required to prevent spoilage through microorganisms.

While it is intended that the compounds described above should be able to be used alone, their use together with other materials known to those skilled in the art to be active against microorganisms is not excluded.

The following example illustrates some specific embodiment of and best modes for carrying out the invention, to which the invention is not limited. All parts are by weight.

Example 1 A lotion was prepared by dissolving in parts of water 5 parts of a product obtained by reacting 1 gram molecule of undecylenic acid with 2 gram molecules of diethanol-amine at C. to C. till the free fatty acid content fell to about 5%. This lotion was suitable for treating skin conditions caused by fungi.

Example 2 Three parts of undecylenic monoisopropanolamide were dissolved in ten parts of isopropyl alcohol at about 30 C. and sprayed onto 97 parts of cosmetic grade talc. The whole was intimately mixed and kept warm during the mixing operation so as to volatilise as much as possible of the alcohol. The resulting powder was suitable as a foot powder for treating conditions such as atheletes foot.

Example 3 Three parts of undecylenic acid monoisopropanolamide are stirred into 92.5 parts of water at 65 C. together with 4.5 parts of sodium N-lauroyl sarcosinate which acts as a dispersing agent. When cool, the resulting product constitutes a very fine dispersion of undecylenic acid monoisopropanolamide which, when first made, is almost transparent. This dispersion can be used for the treatment of skin conditions caused by bacteria or fungi.

Example 4 2 parts of undecylenic acid n-propanolamide, in the form of fine flakes, are added to 97.5 parts of toilet soap flakes on a triple roller soap mill. The soap is a product made from tallow and coconut oil. 0.5 part of a soap perfume having a rose odor is also added. The whole is milled and then fed back into the mill to pass through again and again until the undecylenic n-propanolamide is uniformly dispersed. Four millings in all were adequate. The resulting soap was fed into a soap plodder, extruded, cut and finally stamped as toilet soap tablets in accordance with the usual techniques. The resultant toilet soap has germicidal and fungacidal powers and can be used for preventing or mitigation of skin diseases caused by infection.

Example 5 0.1 part of dichlormetaxylenol together with 2 parts of undecylenic acid monoisopropanolamide are dissolved in 20 parts of propylene glycol monostearate and 5 parts of stearic acid are added, all at 70 C. The whole is poured into 70.9 parts of water together with 2 parts of triethanolamine, all at 55 C. The mixture is vigorously stirred and then cooled with stirring to 25 C. The resulting product is a nearly white cream. This cream is efiective against a very wide range of micro- The efiectiveness of. the undecylenic derivaorganisms. v tive against fungi is supplemented by the etfectiveness of the dichlometaxylenol against bacteria, particularly against gram negative bacteria against which the undecylenic product is less effective.

Whatis claimed is: v

1. A process for combatting micro-organisms, which comprises applying thereto a biocidally effective amount wherein the group C H CO is the acyl derivative of undecylenic acid, R is selected from the group consisting of alkyl and alkylol, and containing up to 4 carbon atoms;;n stands'for an integer of'14 and y is an integer in the range of 1-30.

2. A process for c'ombatting micro-organisms, which comprises applying thereto a biocidally efiective amount of a compound:

* CH CH OH CmHieC ON CHg.CHz.OH

admixed with excess diethanolamine such thatthere is present an excess of diethanolamine about equal to the amount combined in the undecylenic acid diethanolamide.

September 1945, pp. 415425, esp. p. 422.

Broder'sen et al.: Acta Pharmacologica et Toxicologica, vol. 3 (1947) pp. 17-29.

Reinisch at al.:v J. Soc. Cosmetic Chemists, 5: 3, Nov. 1954, pp. 169478; 

2. A PROCESS FOR COMBATING MICRO-ORGANISMS, WHICH COMPRISES APPLYING THERETO A BIOCIDALLY EFFECTIVE AMOUNT OF A COMPOUND: 